4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose | 371164-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose
• 英文别名: (3S)-3-(1-azido-3,3-dimethoxypropyl)-1,4-dioxaspiro[4.5]decane
• CAS: 371164-35-1
• 化学式: C₁₃H₂₃N₃O₄
• 分子量: 285.343
• InChiKey: PJKDKBWCSPVDSM-RRKGBCIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 、 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 以38%的产率得到齐多夫定
  参考文献：
  名称：

  A novel synthesis of AZT

  摘要：

  A novel synthesis of AZT has been achieved from two commercial available products acetaldehyde and D-Mannitol. The originality of the synthesis consists of using the powerful monovinylogation reagent, the 2-lithio-1-trimethylsiloxyethylene, and to introduce the thymine moiety and to build the furanose ring in the same and last step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00695-0
• 作为产物：
  描述：

  4,5-O-cyclohexylidene-2,3-dideoxy-aldehydo-D-glycero-trans-pent-2-enose 在 sodium azide 、 四氯化钛 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 3.0h， 生成 4,5-O-cyclohexylidene-2,3-dideoxy-3-azido-1,1-dimethoxy-D-glycero-pentanose
  参考文献：
  名称：

  A novel synthesis of AZT

  摘要：

  A novel synthesis of AZT has been achieved from two commercial available products acetaldehyde and D-Mannitol. The originality of the synthesis consists of using the powerful monovinylogation reagent, the 2-lithio-1-trimethylsiloxyethylene, and to introduce the thymine moiety and to build the furanose ring in the same and last step. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00695-0

文献信息

• A novel synthesis of AZT
  作者：Christine Gauthier、Yvan Ramondenc、Gérard Plé

  DOI：10.1016/s0040-4020(01)00695-0

  日期：2001.8

  A novel synthesis of AZT has been achieved from two commercial available products acetaldehyde and D-Mannitol. The originality of the synthesis consists of using the powerful monovinylogation reagent, the 2-lithio-1-trimethylsiloxyethylene, and to introduce the thymine moiety and to build the furanose ring in the same and last step. (C) 2001 Elsevier Science Ltd. All rights reserved.